One common method of alkylating organic compounds is by utilizing alkylating agents such as olefins or alkylhalides in the presence of a Friedel Crafts catalyst. One example of alkylating an amine compound using an olefin is described in U.S. Pat. No. 4,322,530. This patent teaches a one-step catalytic method of alkylating a polyamine by contacting a compound having a multiplicity of primary and/or secondary amine groups, a monoolefin, water and carbon monoxide. These components are contacted in the presence of a catalytic amount of a rhodium compound selected from metallic rhodium, rhodium salts, oxides, or carbonyls, which may have phosphines or other ligands present. The reaction is carried out in an inert solvent at temperatures from 50.degree. to 250.degree. C. and pressures from about 30 to 300 atmospheres.
Using an alkylamine as the alkylating agent generally proved to be unfeasible in that the rate of production of the desired alkylated product proceeded at a low rate which slowed, or in some instances, ceased to operate. The slowness of the reaction is due to the fact that the amine group of the alkylating agent poisons the catalyst by the formation of an acid-base compound, the poison thus rendering the catalyst incapable of performing as such.
U.S. Pat. No. 4,430,513 discloses one method in which alkylamines can satisfactorily be used as alkylating agents. Specifically, this patent teaches the self-alkylation of alkylamine compounds which contain at least two alkyl substituents containing from about 2 to 6 carbon atoms. The alkylamine compounds are alkylated in the presence of a metal carbonyl or a metal compound capable of forming a carbonyl at reaction conditions. The reaction is carried out at temperatures ranging from 50.degree. to 300.degree. C. and at high pressures; i.e., between 20 and 300 atmospheres.